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    1. Local experiences/
    2. All experiences/
    3. sailing

    Best results for Sailing

    Showing 337-360 of 404 results
    Key West 1.5-Hour Classic Day Sailing Cruise
    Key West, FL

    Key West 1.5-Hour Classic Day Sailing Cruise

    Sail Key West on Schooner America 2.0 with complimentary soft drinks

    Sail Key West on Schooner America 2.0 with complimentary soft drinks
    4.9 • 592 reviews
    $64/ person
    Salem Harbor Sunset Sail on 1812 Schooner
    Salem, MA

    Salem Harbor Sunset Sail on 1812 Schooner

    Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.

    Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.
    5.0 • 535 reviews
    $49/ person
    Private Sailing Lesson in Nantucket
    Nantucket, MA

    Private Sailing Lesson in Nantucket

    Learn to sail with a private instructor at Jetties Beach

    Learn to sail with a private instructor at Jetties Beach
    5.0 • 2 reviews
    $265
    Youth Private Sailing Lesson at Jetties Beach
    Nantucket, MA

    Youth Private Sailing Lesson at Jetties Beach

    Build sailing skills with a private youth lesson for up to 3 sailors

    Build sailing skills with a private youth lesson for up to 3 sailors
    5.0 • 2 reviews
    $212
    Guided Hobie Cat Sail with Captain Included
    Grapevine, TX

    Guided Hobie Cat Sail with Captain Included

    Glide across Grapevine Lake on a guided 1-hour Hobie Cat sail with captain included.

    Glide across Grapevine Lake on a guided 1-hour Hobie Cat sail with captain included.
    4.5 • 1.3K reviews
    $65/ person
    Sail to Wood Island Lighthouse Tour From Kennebunkport
    Saco, ME

    Sail to Wood Island Lighthouse Tour From Kennebunkport

    Sail to Wood Island and tour inside the lighthouse and keeper’s house

    Sail to Wood Island and tour inside the lighthouse and keeper’s house
    5.0 • 382 reviews
    $395/ person
    Full-Day Lake Erie Sailing Charter
    Sandusky, OH

    Full-Day Lake Erie Sailing Charter

    Sail Lake Erie for about 8 hours on a private charter for up to 6 guests

    Sail Lake Erie for about 8 hours on a private charter for up to 6 guests
    5.0 • 41 reviews
    $1,537
    Cruise Waikiki For Friday Fireworks & Sunset
    Honolulu, HI

    Cruise Waikiki For Friday Fireworks & Sunset

    Sail out for Waikiki’s Friday fireworks with sunset views

    Sail out for Waikiki’s Friday fireworks with sunset views
    4.9 • 1.5K reviews
    $72/ person
    St. Augustine Nights of Lights Sailing Tour
    St. Augustine, FL

    St. Augustine Nights of Lights Sailing Tour

    Sail a 35-foot yacht and admire St. Augustine's dazzling Nights of Lights

    Sail a 35-foot yacht and admire St. Augustine's dazzling Nights of Lights
    5.0 • 740 reviews
    $145/ person
    Sail on a Private Charter in Waikiki
    Honolulu, HI

    Sail on a Private Charter in Waikiki

    Customize your private Waikiki charter for groups up to 40

    Customize your private Waikiki charter for groups up to 40
    4.9 • 741 reviews
    $1,826& up
    BYOB Sunset Cruise with Live Music or DJ in Waikiki
    Honolulu, HI

    BYOB Sunset Cruise with Live Music or DJ in Waikiki

    Sail Waikiki at sunset with live music or a DJ on a BYOB catamaran with appetizers

    Sail Waikiki at sunset with live music or a DJ on a BYOB catamaran with appetizers
    4.8 • 663 reviews
    $122/ person
    Maui Sunset Sail on a Floating Tiki Bar Catamaran
    Kihei, HI

    Maui Sunset Sail on a Floating Tiki Bar Catamaran

    Sip island cocktails and savor appetizers as you sail at sunset aboard a Hawaiian-built catamaran

    Sip island cocktails and savor appetizers as you sail at sunset aboard a Hawaiian-built catamaran
    $138/ person
    The Locals Island Charter
    Pensacola, FL

    The Locals Island Charter

    Sail to a secluded beach near Fort McRee for swimming, paddleboarding, and lunch on a private 6-hour charter

    Sail to a secluded beach near Fort McRee for swimming, paddleboarding, and lunch on a private 6-hour charter
    5.0 • 16 reviews
    $1,344
    Dolphin Sightseeing Sail Aboard the Daydreams Sailboat
    Panama City, FL

    Dolphin Sightseeing Sail Aboard the Daydreams Sailboat

    Sail Grand Lagoon and Shell Island with complimentary drinks while spotting dolphins

    Sail Grand Lagoon and Shell Island with complimentary drinks while spotting dolphins
    4.9 • 2.9K reviews
    $88/ person
    Sunset & Fireworks Sail in St. Augustine
    Saint Augustine, FL

    Sunset & Fireworks Sail in St. Augustine

    Sail at sunset with live music, drinks, and St. Augustine fireworks views

    Sail at sunset with live music, drinks, and St. Augustine fireworks views
    4.8 • 231 reviews
    $186/ person
    Cruise St. Augustine Nights Of Lights On A Sailboat
    St. Augustine, FL

    Cruise St. Augustine Nights Of Lights On A Sailboat

    Sail the Nights of Lights with dessert and a festive drink

    Sail the Nights of Lights with dessert and a festive drink
    5.0 • 740 reviews
    $668& up
    Sail to Wood Island Lighthouse Private Tour in Maine
    Saco, ME

    Sail to Wood Island Lighthouse Private Tour in Maine

    Sail to Wood Island and tour inside the lighthouse and keeper’s house

    Sail to Wood Island and tour inside the lighthouse and keeper’s house
    5.0 • 382 reviews
    $1,707& up
    Salem Sound Sail Aboard the Schooner Fame
    Salem, MA

    Salem Sound Sail Aboard the Schooner Fame

    Hands-on 1812-style sail with engaging crew and scenic Salem Sound views

    Hands-on 1812-style sail with engaging crew and scenic Salem Sound views
    5.0 • 535 reviews
    $37/ person
    Sail Repair and Sail Making Course
    Barrington, RI

    Sail Repair and Sail Making Course

    Learn to design, build, and repair sails in a hands-on two-day class

    Learn to design, build, and repair sails in a hands-on two-day class
    4.9 • 67 reviews
    $625/ student
    Cruise Grand Traverse Bay on a 6-Hour Private Sail
    Traverse City, MI

    Cruise Grand Traverse Bay on a 6-Hour Private Sail

    Private 6-hour sail for up to 6, with time to raise sails and take the wheel

    Private 6-hour sail for up to 6, with time to raise sails and take the wheel
    4.9 • 527 reviews
    $812
    Weekend Sailing Cruise From Barrington to Block Island
    Barrington, RI

    Weekend Sailing Cruise From Barrington to Block Island

    Sail a 42-foot boat to an island while you build skills with an instructor

    Sail a 42-foot boat to an island while you build skills with an instructor
    4.9 • 67 reviews
    $1,150/ cabin
    4-Hour Sailing Lesson on Narragansett Bay
    Barrington, RI

    4-Hour Sailing Lesson on Narragansett Bay

    Practice sailing skills with an instructor on Narragansett Bay

    Practice sailing skills with an instructor on Narragansett Bay
    4.9 • 67 reviews
    $265/ person
    2-Hour Brunch Sailing Cruise in Seattle
    Seattle, WA

    2-Hour Brunch Sailing Cruise in Seattle

    Sail Seattle’s harbor and enjoy a brunch buffet on a tall ship

    Sail Seattle’s harbor and enjoy a brunch buffet on a tall ship
    4.8 • 360 reviews
    $92/ person
    Sunset and Dolphin Watch Sailing Cruise on Island Time II Catamaran
    Panama City Beach, FL

    Sunset and Dolphin Watch Sailing Cruise on Island Time II Catamaran

    Sail calm waters to spot dolphins and enjoy a Gulf sunset with dancing and games

    Sail calm waters to spot dolphins and enjoy a Gulf sunset with dancing and games
    4.8 • 1.7K reviews
    $58/ person
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